Top 15 Most Desirable Places to Live in Connecticut

Connecticut is one of the most delightful states in the United States. With a rustic combination of coastal towns and rural retreats, this region of New England presents numerous appealing aspects. Unlike many other US states, Connecticut boasts access to the coastline, attracting surfers, beach enthusiasts, and sun seekers. While the Atlantic Coast sometimes experiences harsh weather, the sunny days in Connecticut are exceptionally beautiful.

From New Haven to Mystic, Connecticut consistently offers new discoveries. Mystic, in particular, is renowned for its Seaport Museum, which features historic sailing vessels, as well as the Mystic Aquarium, home to Beluga whales.

Are you intrigued by Connecticut?

Regardless of your eventual destination in this area, certain essential criteria for your new residence should be considered. Factors such as access to quality public education for families with young children and convenient access to transportation routes for commuters are critical aspects to contemplate.

To assist in your exploration, we have compiled a list of the 15 best places to reside in Connecticut, providing insight into your possibilities within this remarkable American state.

1. Simsbury

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Ranked as the top place to live in Connecticut, Simsbury is an award-winning town that has been federally designated as a “Preserve America” community.

This picturesque town features historic homes, dining options, farms, and abundant green spaces. With numerous hiking trails, a river, and a bike path, Simsbury provides a wealth of outdoor recreational activities for residents.

It is also home to the largest tree in Connecticut, the Pinchot Sycamore. With a population exceeding twenty-four thousand, Simsbury boasts an excellent public school system, making it an ideal environment for families, and maintains a robust economy.

Combining outdoor activities, superior education facilities, and healthcare services, Simsbury is an exceptional choice for families seeking a new home.

Entertainment & Activities

Some of the noteworthy activities in Simsbury, Connecticut, include:

• Heublein Tower
• Talcott Mountain State Park
• Old Drake Hill Flower Bridge
• Simsbury Historical Society
• Phelps Tavern
• Simsbury Center Historic District
• Stratton Brook State Park
• Rosedale Farms & Vineyards
• The Storyteller’s Cottage
• Pinchot Sycamore
• Simsbury Meadows Performing Arts Center
• Cycling
• Flamig Farm
• Roaring Brook Nature Center
• Simsbury Farms Golf Course

2. New Canaan

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Located in Fairfield County along the Fivemile River, the town of New Canaan is recognized as one of the premier locations to reside in Connecticut. The town is characterized by its rural ambiance and modern architecture.

Renowned for being an excellent place to raise a family, New Canaan attracts a variety of notable residents from diverse professions. Moreover, the New Canaan Center offers residents a multitude of retail options.

The streets of New Canaan are adorned with boutique shops, high-end retailers, home goods outlets, dining establishments, and much more. With a population of around twenty thousand, popular events in New Canaan include the Annual Summer Village Fair and Sidewalk Sales.

If you seek a stylish and sensible New England town, New Canaan is an ideal choice.

Entertainment & Activities

Some of the renowned attractions in New Canaan include:

• The Philip Johnson Glass House
• Waveny Park
• Silvermine Arts Center
• Grace Farms
• New Canaan Historical Society
• New Canaan Nature Center
• Carriage Barn Arts Center
• Mead Memorial Park
• Browne Wildlife Sanctuary
• Summer Theatre of New Canaan
• Irwin Park
• Mill Pond Park
• St Mark’s Episcopal Church
• Stamford Museum & Nature Center
• New Canaan Halloween Parade

3. Old Greenwich

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Old Greenwich is an attractive waterfront community, renowned as one of the finest places to live in Connecticut. This New England town is situated on a peninsula and has a population of over six thousand inhabitants.

As you navigate through the community, you will encounter vibrant streets and picturesque coastlines. South Beach Avenue features numerous local businesses that contribute to the village’s character. Winding roads will lead you to the beautiful shoreline.

Old Greenwich emphasizes community engagement, with closely positioned residences where neighbors often relax on porches and actively participate in maintaining the beauty of their environment.

The area features a blend of antique residences and contemporary mansions, many of which command prices above one million dollars. Northern districts offer cape cod and colonial homes for slightly less. If you have the means, Old Greenwich could be your perfect home.

Entertainment & Activities

Some esteemed activities in Old Greenwich include:

• Putnam Cottage
• Flinn Art Gallery
• Bruce Museum
• Greenwich Point Park
• Greenwich Audubon Center
• Montgomery Pinetum & Pomerance Park
• Mianus River State Park
• Hiking in Babcock Preserve

4. Weatogue

Source: Craig Hallett / Flickr

As a small suburb of Hartford, Weatogue has a village-like atmosphere with a population of only around 3,000. Housing prices in this area remain relatively affordable, making it accessible for the average working American.

Consequently, Weatogue has gained recognition as one of the best locations in Connecticut to purchase a home.

The community enjoys exceptionally low crime rates, likely attributed to its small size and the friendly demeanor of its residents. This neighborhood welcomes families, retirees, and young professionals alike.

Entertainment and Activities

Some of the leisure activities available in or near Weatogue comprise:

• Roaring Brook Nature Center
• The Children’s Museum
• The Mark Twain House
• Wolcott Park and Spray Pad
• Bushnell Park and Carousel
• Weatogue Park
• Paw Meadow Dog Park
• Granbrook Park
• The Brewery at Maple View Farm

5. Weston

Source: Dougtone / Flickr

Located approximately forty-five miles from New York City, Weston is a unique, sophisticated community with over ten thousand residents. The town features a robust educational system, minimal commercial development, and abundant open spaces, making it an excellent place for families.

In Weston, residents enjoy minimal traffic, contributing to its peaceful ambiance. When individuals need to dine or shop, they can easily access the Weston Town Center, which offers a local food market, bank, post office, restaurant, and gas station.

This closely-knit community has a history of volunteerism and extends a welcoming hand to neighbors in times of need. If you desire a tranquil town away from the city’s hustle and bustle, Weston is a truly outstanding option to consider.

Entertainment & Activities

Some of the popular activities in Weston include:

• Devil’s Den Preserve
• Coley Homestead
• Weir Farm National Historic Site
• Lachat Town Farm
• Trout Brook Valley Preserve
• Norfield Congregational Church
• Katharine Ordway Preserve
• Amber Falls
• Great Ledge
• Bisceglie-Scribner Park
• Bradley Edge Tool Company Historic District
• Ambler Farm
• Weston Farmers’ Market
• Wilton Playshop

6. Avon

Source: Dougtone / Flickr

Located in the Farmington Valley and bordered by the Talcott Mountain range, Avon is recognized as one of the top locations to reside in Connecticut. For those seeking a peaceful lifestyle, Avon is an ideal destination.

This tranquil town offers superior services, excellent educational institutions, and ample outdoor recreational opportunities. Just a short drive away in West Hartford, residents can access shopping, dining, attractions, and local businesses. Centrally located within Connecticut, Avon allows access to any part of the state within an hour and the major cities within two hours.

If you appreciate outdoor recreation, Avon boasts numerous parks and trails for hiking and walking. Residents can participate in seasonal classes and activities, as well as enjoy two local golf courses.

For those who wish to unwind in a peaceful environment while having the option for day trips, Avon is the perfect residence.

Entertainment & Activities

Some of the popular attractions in Avon include:

• Avon Old Farms School
• Farmington Valley Arts Center
• Knit & Pearls
• Blue Fox Run Golf Course
• Pine Grove School House
• Horse Guard State Park
• Susan Prentice Studio & Gallery
• Max a Mia
• Seasons Restaurant at Avon Old Farms Hotel
• The Elephant Trail

7. Glastonbury

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Glastonbury serves as another suburb of Hartford and is notable for its well-rounded offerings. The western border of Glastonbury is adorned by the winding Connecticut River.

Founded in 1693, with the first settlers arriving in 1636, Glastonbury features classic New England houses and offers great value for money, like other suburbs such as Avon and Weatogue.

With a population exceeding thirty-five thousand, Glastonbury residents benefit from access to numerous historic sites, nature parks, the Connecticut River, and various programs hosted by the town.

Parents seeking exceptional public school opportunities for their children will find Glastonbury to be an excellent choice, as it houses one of the largest school districts in Connecticut, featuring 46 outstanding educational institutions.

Entertainment & Activities

Highlights of activities in Glastonbury encompass:

• Riverfront Park
• Glastonbury Historic District
• Apple Harvest & Music Festival
• Rocky Hill-Glastonbury Ferry
• Historical Society of Glastonbury
• Blackledge Falls
• Welles Turner Memorial Library
• Dondero Orchards
• Crystal Ridge Winery
• Rose’s Berry Farm
• Webb-Deane-Stevens Museum
• Minnechaug Golf Course
• Central Rock Gym
• Welles-Shipman-Ward House
• Cotton Hollow Preserve

8. Ridgefield

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Ridgefield, with a population exceeding twenty-five thousand, is recognized as one of the premier places to live in Connecticut. It features the historic Main Street, exceptional public schools, and has been labeled the safest town in the state.

Residents enjoy diverse shopping options at unique boutiques, local stores along Danbury Road, and a variety of dining experiences. With its array of offerings in a charming setting, many families are drawn to Ridgefield as their home.

Entertainment & Activities

Highlights of activities in Ridgefield encompass:

• Keeler Tavern Museum and History Center
• Weir Farm National Historic Site
• Ridgefield Playhouse
• Aldrich Contemporary Art Museum
• Main Street
• Prospector Theater
• ACT of Connecticut
• Garden of Ideas
• Devil’s Den Preserve
• Pine Mountain/Hemlock Hills
• Ridgefield Historical Society
• Saltana Cave
• Seth Low Pierrepont State Park
• Hammond Museum and Japanese Stroll Garden
• Saugatuck Reservoir

9. Greenwich

Source: James Kirkikis / shutterstock

Known as one of the state’s oldest towns, Greenwich has been recognized as one of the finest places to reside in Connecticut. Located just a short fifty-minute train ride from New York City, Greenwich combines the charm of New England with the conveniences of urban living.

The area’s scenic landscapes evoke memories of Europe, while its dining and cultural scenes may remind you of Manhattan but without the traffic. Many affluent residents who work in Manhattan reside in Greenwich, taking advantage of its accessible commute.

While wandering through town, you will observe well-maintained gardens, historic homes, and impressive mansions. With a population exceeding sixty thousand, Greenwich offers far more than an average town and has been rated as one of the most picturesque towns in Connecticut.

Entertainment & Activities

Some notable attractions in Greenwich are:

• Bruce Museum
• Greenwich Avenue Historic District
• Audubon Center
• Bush-Holley House
• Greenwich Point Park
• Island Ferries
• Fjord Fish Market, Cos Cob
• Diane’s Books
• Greenwich Polo Club
• Montgomery Pinetum
• Neuberger Museum of Art
• Donald M. Kendall Sculpture Gardens
• Bruce Park
• Flinn Gallery
• Putnam Cottage

10. Woodbridge

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With a population exceeding nine thousand, Woodbridge is enveloped in lush countryside, characterized by large single-family homes on expansive lots.

The town provides an excellent educational system, abundant walking trails, a variety of recreational programs, and a quaint small-town ambiance. Additionally, local businesses are conveniently located close to essential transportation routes, including I-95 and Route 8 Highway.

Residents benefit from close proximity to healthcare, entertainment, business districts, and educational facilities. If you are contemplating a move to a cozy small town, Woodbridge presents an exceptional option.

Entertainment & Activities

Some intriguing activities in or near Woodbridge comprise:

• New England Brewing Co
• The Tradition Golf Club at Oak Lane
• Savino Vineyards
• Palestine Museum
• Amity Bowl
• SeaQuest Connecticut
• Brookside Farm Market
• Yale Peabody Museum
• Quassy Amusement & Water Park
• West Rock Ridge State Park

11. Newfield

Niche has recognized Newfield as one of Connecticut’s most desirable locations. The urban atmosphere here allows many residents to rent their homes.

Newfield boasts numerous parks, dining options, and coffee shops, rendering it an excellent locale for young professionals and families alike. Nearby Stamford hosts many prominent corporations.

In proximity, you will find the Stamford Museum & Nature Center, Cove Island Park, and other beautiful beaches and hiking trails.

Entertainment & Activities

Some popular activities in Newfield include:

• Stamford Museum & Nature Center
• Cove Island Park
• Curtain Call, Inc
• The Ferguson Library
• First Presbyterian Church
• The Palace Theatre
• Half Full Brewery
• Bartlett Arboretum
• Captain John’s Tiki Tours
• Fort Stamford Park

12. Darien

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Darien, with a population of approximately twenty-two thousand, is the smallest city along Connecticut’s coastline and is also among its wealthiest communities. It features two railroad stations that provide access to Manhattan’s Grand Central Terminal.

Positioned between Stamford and Norwalk, Darien offers various outdoor recreational activities, including public beaches and country clubs. Additionally, its schools are ranked among the highest in Connecticut.

The town’s natural environment and ambiance are enjoyed by its residents. With spacious homes and coastal features, Darien is one of the most desirable places for families to live in Connecticut.

Entertainment & Activities

Some prominent activities available in Darien include:

• Pear Tree Point Beach
• Darien Historical Society
• Darien Library
• Cherry Lawn Park
• The Mather Homestead
• Cove Island Park
• The Maritime Aquarium at Norwalk
• Weed Beach
• Waveny Park
• Tilley Pond Park
• Lock City Brewing Company
• Geary Gallery
• Lockwood-Mathews Mansion Museum
• South Norwalk Historic District (SoNo)
• Salt Cave of Darien

13. West Hartford

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If you are seeking a diverse community in Connecticut that seamlessly blends urban and suburban experiences, West Hartford is an ideal choice. This area fosters a supportive community, offering excellent public education, secure neighborhoods, and various programs catering to all ages.

West Hartford is an inviting and reasonably priced suburb in relation to the state capital, especially when compared to places like Darien. The median property value here remains much more attainable for the average working family.

This locale is popular among millennials, likely due to its relatively lower housing prices.

Local residents often express enthusiasm for the community and regard it as a prime location for raising families, complemented by safety and a wide array of activities suitable for all ages, including hiking, swimming, and social clubs.

Entertainment & Activities

Some favored attractions in West Hartford include:

• Elizabeth Park
• West Hartford Center
• Blue Back Square
• Noah Webster House & West Hartford Historical Society
• The Children’s Museum
• Art Museum, University of Saint Joseph
• Westmoor Park
• West Hartford Reservoir
• Playhouse on Park
• Westfarms
• Wolcott Park
• Fernridge Park
• Mark Twain House & Museum
• Thomas Hooker Brewery
• Iwo Jima Survivors Memorial Park

14. Riverside

Source: www.elliman.com

Riverside is an extremely affluent suburb of Greenwich and part of the greater New York City metropolitan area. While real estate prices here often exceed one million dollars, the properties themselves are quite remarkable.

With a median household income that surpasses the average, many residents choose to finance these properties through mortgages, which, in the broader scope of things, is not a major burden.

In many respects, Riverside’s public educational offerings align with the state’s high standards, making it a viable option for families who prioritize their child’s education.

Entertainment & Activities

Notable attractions and activities in Riverside include:

• RPM Raceway
• Greenwich Point Park
• Cos Cob Park
• Cove Island Park
• Greenwich Wine and Food Festival
• Playland Park
• Northern Lights Bar and Lounge

15. Cos Cob

Source: wikimedia.org

Completing our list is Cos Cob, a part of the town of Greenwich. In this community, most homes are single-family residences situated on large lots, typically featuring swimming pools.

North of Cos Cob Harbor, Cos Cob Park offers miles of walking trails, a playground, a pavilion, and a 9/11 memorial, providing various recreational opportunities. Additionally, Cos Cob schools have earned high ratings, rendering it an ideal locale for raising a family.

Despite its smaller population, the school district comprises only seven schools, all of which maintain excellent standards, consistent with Connecticut’s reputation for quality education.

Entertainment & Activities

Some notable attractions and activities in Cos Cob include:

• Bush-Holley House Museum
• Greenwich Botanical Center
• Fjord Fish Market